Wall Street Playboys - Advice from Real Wall Street Professionals

Is It Time To Take a Risk?

We get a lot of questions about how to make a comeback if they’re age XX or if they should quit their jobs today. Unfortunately, they never address the core issue of *risk*. Risk is all about foregone opportunities. If the foregone opportunity was nothing to begin with, it’s time to jump ship. If your foregone opportunity is a million dollars, it’s time to review the risk profile.

Life Risk – Unacceptable

The first type of risk is the most important: risk of losing your entire life. We’re not talking about getting hit by a car or a bus which could happen as a freak event. We’re talking about making decisions that practically guarantee you’re going to be stuck relying on other people (borderline welfare). Or worse, making other people reliant (unable to support a family).

The Dead-End: If you’re making $60K a year in salary (total compensation), you’re solidly in dead-end risk territory. You have to get out. It doesn’t matter if you’re worried about paying the bills. Your unemployment checks would practically offset your cost of living anyway.

You’re not allowed to have any fun if the current future says “dead-end”. This means no partying at the club. No drinking with friends after work and absolutely no right to live alone. You’re in hell and the only way out is to switch into a career (at minimum) or start scaling a business *starting yesterday*

In general, most individuals are risk averse, constantly worried about being able to find the next position. It doesn’t add up. If you’re making $5K a month (pre-tax!), there is just no wiggle room for error anymore, your entire life is at risk.

Shackles: This is also known as “painting yourself into a corner”. We talk a lot about uncomfortable topics such as family members holding you down and this is no different. People shouldn’t be having families if they can’t afford them. This is just another anchor in life that can cause a material amount of stress over the next several years. No different than getting legally married followed by a divorce (1/2 of your income for life is certainly a shackle)

A similar less emotional example is debt load. Levering up a balance sheet (your net worth) is a dangerous activity. If total debt payments are not covered by investment income the downside is far too large. This is a severely conservative approach since you don’t want to make a life changing mistake into the red. Total recurring income “passive income” needs to be higher than the total debt payments.

“There are two ways to conquer and enslave a country. One is by the sword the other is by debt.” – John Adams

Paying the Life Toll: While we focus on efficiency, there is no way to avoid paying the toll. The Toll is 3-5 years of working 60-80 hours per week. That is not a typo. Everyone in their 20s must pay this toll if they want to become financially successful and the longer they wait the more it becomes a real life risk.

Why is it a life risk? Well, there is an interest rate on that 60-80 hour a week payment owed to the Money Gods. The longer someone waits the more hours they must pay back. If someone pays the life toll of 60-80 hours per week for 3 years in the age range of 20-22, that toll now becomes 5 years if someone starts at age 30. It continues to increase until the toll is paid.

“Quality is never an accident. It is always the result of intelligent effort.” – John Ruskin

Summary of Life Risks: Under no circumstances do you take a life risk. What does this mean?

Dead-End Issues:

– If you’re working a salary (job) then you’re going to work 40 hours per week after workAND you are going to attempt to work while at your job to generate money from a side business. There is *no excuse* here and no exceptions. If an incorrect career choice was made then you’re 100% forced to start a business while simultaneously transitioning your skills toward a career (a dual process)

– If you’re older then your choice is limited to just one: start a business with recurring revenue. There is no other choice. There is no lower risk choice because the price was never paid and going down the wrong path means you’re running back to the starting line to take it into a different direction! It is the only way to reverse the course.

Shackles:

– This is boiled down to emotional control. Ask if the decision makes financial sense and if it doesn’t then there is no reason to do it. We don’t care if everyone else is doing it (buying a home, signing governmental marriage contracts). That’s not a valid reason because the vast majority of people never become financially independent in the first place. Make no mistake, your life is a business until you’re financially independent.

Paying the Toll:

– Well if you’re doing the first two, killing all dead-end items and avoiding catastrophic financial mistakes you’re not going to have very much free time. Why? You’re extremely busy paying the toll. Your life consists of eating, drinking, working out and sleeping. Can’t go broke if all your time is spent producing something to make you more money.

Opportunity Risk – Acceptable

Everyone is different. We’ve found that somewhere around a million dollars in liquid net worth makes you value your time significantly more. If you’re part of the growing online frugality group it’s less and if you’re in the group that realizes life without work is boring… it’s much higher than a million bucks (yes we’re in group 2!).

Loss of One Time Investments: If you’re making money with a business outside of a steady paycheck, we can practically guarantee money will be lost at some point. Either due to traffic that isn’t converting, a product that is mis-priced or both. The key is to make sure you’re making the right risk to reward decisions. Was the opportunity cost superior? If not it was still the right decision even if money was lost.

As an example, if you have located a specific niche for a diet related product that could generate $100K in income per year… It is absolutely worth the $50K start up cost. If the idea would require an unchanging website (not a content website like a blog) then your upside is already 100% in year one ($50K in to get $100K back). More importantly, if the product and targeted ad campaign works out, this is going to be forever. You’re going to clean up by making $100K per year for an initial $50K outlay. Overall, all you need is a 3-5% success rate (probably less) for you to go ahead and invest the $50K today.

The key is this: will the upfront costs lead to long-term revenue generation versus straight time for money exchanges (hourly income). If so it is worth the risk.

Losing Your Best Years: This was partially covered in the greatest book ever written “How to Get Rich” by Felix Dennis. Eventually you’ll reach a point where making additional money is eating up too much of your time. When you’re 20 there is no reason to do anything besides make money (assuming you want to be successful) so grinding away for 80 hours a week makes a lot of sense. When you start creeping up in age to 30, 35, 40 and beyond… it becomes significantly less clear if the effort is worth it.

We only get one shot at life (for now!) so we should live appropriately. If you’re never touching the principal (cost of living income) then it may not make sense to continue putting in those long hours. Don’t get us wrong. The game never really ends. If your personality type allowed you to crank out 80 hours per week in your 20s, you’re not going to sit around the house watching sports all day. Chasing an extra line of income when you could be traveling the world and avoiding regret is significantly more valuable.

Declining Income Risks: There are several industries with material declining income profiles. Look no further than our post on the future of Wall Street where we predict declines in Equities related positions. The interesting point here is the value in a declining business. This is no different than buying a company in a dying industry. There is still a ton of value in riding the declines to zero!

Specifically, if you find an opportunity to invest money into a declining business, it may be worth it. The trick is making sure that the business will generate enough cash flow to offset the inevitable declines. Calculate all of the future income and see if you can net a material positive return. It sounds risky at first glance… But… No one wants to deal with a declining business which creates an opportunity for a major bargain.

Summary of Acceptable Risks: We’ve lost tons of money in the past off of ideas that never worked. We don’t think this will be any different for other people going down the exact same route. You’ll lose money (you’ll get it back), You’ll value your time more and of course, you’ll find ways to bargain hunt for terribly run businesses that no one wants to deal with. Importantly, these *acceptable* risks should never create a life risk. You’re not going to throw down money in excess of your cost of living income into any venture since it’ll break the bank if mis-execution occurs.

What isn’t a Risk?

We’ve heard of several that don’t make any logical sense. Risk has nothing to do with feelings and is 100% related to an impact to your standard of living. If it does not impact your standard of living it’s not a risk.

Fear of Social Loss: This blog is a good example. We receive comments that state they are not willing to participate in our Facebook Q&A (March 16, 8PM EST) since they don’t want to “like the page”. All of these people will fail (so yes feel free to like the page to improve your chances of succeeding!). There is no doubt in our mind that they will fail because following a blog is not going to impact your future at all (it is not a risk). In addition, we’ve got enough traffic here that it’s becoming normal to visit the page.

Secondly, we learned that many people spend 1-2 hours per day on Facebook! Think about that. They don’t have any money but are willing to spend more time on Facebook to improve their “social status ranking”. If impressing peers is the strategy to get rich, we have several luxury handbags and cars to sell them into slavery.

Serviceable Debt: This is also not a risk. If you’re taking income in the form of dividends to offset the payments of a mortgage, it is not a risk at all. Debt for home equity is typically not enough to be considered a risk unless you’re relying on active income to make the payments. This means mortgages (for our smart readers) will not be considered a risk. Inflation will cause the asset to appreciate over the long-term making the minimal amount of debt a lever for you over the long-term.

Getting Laid Off: This also isn’t a real risk. If you’ve built skills that are transferable a layoff (which occurs to practically everyone at least once) is not a risk. Transferable skills allow you to find work elsewhere and *ideally* allows you to have more free time (temporary) to work on your business venture. Saying that working on a side business will hurt work performance leading to a layoff… well… it doesn’t matter. If you’re committed the results will absolutely come through over time.

Concluding Remarks

Under no circumstances do you ever take a life risk. Ever. By avoiding *life risks* you can sleep soundly knowing that you’ll eventually get there (financially independent). Once you’ve reached that saturation point it’s time to move toward multiple acceptable risks.

In terms of incorrect choices, we’ve found that the most common one is avoiding the toll. Paying the toll is equivalent to saving up for a plane ticket across the country. If you save up early (20s) you get to board the plane. If someone avoids paying the toll until they are older, they are now physically biking across the country. Sure, it is possible to hit the ball out of the park your first attempt at a later age, however, the biking example vs. boarding a flight is a representation of how painful it will be (mentally and physically).

As a note we’ll likely be producing more here as we work on releasing our product (Efficiency), the Death Knell to the Men’s Self Improvement Industry

Comments

Will never understand those that drink beers with the guys/coworkers after work and watch sports/Netflix all weekend when they are 27 working a dead-end job. Is it just innocent ignorance, or a true lack of care.

This post could not have come at a better time. To extrapolate from my comment on the last post, the position I’m taking at the boutique PE firm; while it only pays 1/2 a typical PE salary, It will allow me to build transferable skills and is only 40 hours a week(not including live deals). No reason why I can’t spend another 40 hours building my own business!

The toll represents one of the greatest universals out there… It is a natural wall standing in the way of something unnatural (wealth), and only after knocking that wall down through repeated effort is any reward earned. The greatest part is that quite obviously, almost no one is willing to pay.

The bolded section at the bottom gave me a laugh. Keep up the great work!

Oh there is nothing to laugh about. It’ll basically show that everything can be done in one product (more concise) and people have been wasting $20-50 a pop on items that will be explained in a single chapter.

22 years old, own a landscaping service company that grossed nearly $100K last year and just took over an existing tree farm business for no money down with a creative finance deal. Going to combine the two businesses and add on some other enterprises as well.

Entrepreneurship is difficult as hell, but I’d rather compress the pain into a few short years in my own company – better than toiling away at somebody else’s company until I’m 65 in return for a golden watch.

The more people I talk to others business and careers, the more I see how people end up unhappy later in life. Nobody wants to put in the painful work now… we’re a generation of instant-gratification-fueled softies.

I’m going to keep grinding and really appreciate the light you guys shed on these subjects. Thanks for the work you do. Keep crushing it!

lol at the golden watch part. I remember that I went to my company christmas party one year, this one guy that had worked at the company for like 20 plus years(I think almost 30 or more) was given a gold watch and everybody cheered for him and all. Couple years later, a lot of the people in the company were fired, including the guy. what a joke.

I got hit with a double whammy on my upbringing, helicopter parents forcing me down a largely unprofitable career path while also restricting me socially. Went to a school where Greek Life was a big deal so I didn’t get to enjoy the fun of college but the depression led me to getting bad grades too so screwed there. Finally got it together and am breaking into sales now thanks to reading this blog but I am a 24 year old virgin.

Spent over a year after college unemployed and living at home with toxic parents, finally grew the balls to tell them to fuck off and will be leaving soon.

The worst part is that I am stuck in a very assbackwards part of the country and though I will be moving to a bigger city in the region, it’s still going to be full of your bible thumping self-righteous types.

By 26 I should break the 60k barrier or make possibly even more but the thought of leaving my 20s a virgin is very disturbing to me. I live in the US and it’s not like seeing an escort is legal in my area.

Just trying to balance that part of life with working hard, it seems like my 20s are going to suck.

Love it especially the part of social media/bars this past sept deleted all social media except twitter (news and to follow you guys) best decision. Have more time to focus on stuff that really matters. Had a few friends ask why did I do it? I simply responded it wasn’t making me any money. The looks that I got…

– Twitter: Follow @WallStPlayboys
– Facebook: recently re-activated to take part in Q+A’s and run facebook ads (building a brand)
– Instagram – keep on top of latest style to improve my looks/appearance

Currently stay in Hong Kong for a while where competition is extremely high. Income is not as lucrative as in the US (except for the ibank… it should be quite similar anywhere?). I’m gonna practice sales pretty soon and the only path to be *successful* is either real estate or finance (they call it London Gold here)

At an office I worked out of, there were many desks in a congested area, and then one isolated desk in the basement.

It was colder than the other area, and near a bathroom where the employees would got to take a shit.

And every one of the people there disliked it because it was so isolated.

I took that desk, kept an extra jacket down there, made sure to remind people to use the fan when they used the bathroom.

I could care less about the “negative” of being isolated, I loved it.

Everyday during my lunch I’d read and read all this material related to my industry. During the working day I would be focused and producing.

The other people there would talk and bullshit with each other, during lunch and even during the working day when they should be focused.

After six months I was telling the owner things he didn’t know or had forgotten. Everyone in the office would come to me with their unsolvable issues (while simultaneously emotionally distancing themselves from my knowledge by saying I was “book smart” etc.).

I was once asked by the owner if I needed any help, as he was doing his rounds and checking in with people’s work.

I answered matter of factly “Nope, I’m on top of everything”.

He was surprised, I don’t think he was used to hearing it. Especially with the band of Regulars upstairs. “Really, are you sure.”

“Yeah, I’m positive. Thank you though.”

The lesson being if you can find a practical way to isolate yourself from the Regulars, that will give you even more room to develop / work on your business, so keep an eye out for any opportunities like that. Even if it means you have to remind people to use the fart fan!

Been reading your blog for the last two years – I show it / mention it to friends of mine but most of them never get back to me (normal people)?

Thank to your help I recently secured a NYC MM IBD summer analyst internship. Looking forward to paying the toll, but know that starting a business is the only way to beat the masses, even the ones on Wall Street?

Great post as usual WSPs . As a 22 year old with a strong talent in math, accepted for a math masters in Cambridge (Part III), I am really thinking of how to avoid the Dead End. Do you think becoming a Quant is a good & realistic option? Other options you would recommend?

28 year old here, did not realize that I was trading my time for money at the beginning, I got too comfortable with my life and now have woken up. I am currently dating a girl/entrepreneur who want to succeed just as much as I do. I think it is really helping me being around her.

I resonate a lot with this paragraph you wrote “You’re not allowed to have any fun if the current future says “dead-end”. This means no partying at the club. No drinking with friends after work and absolutely no right to live alone. You’re in hell and the only way out is to switch into a career (at minimum) or start scaling a business *starting yesterday*”

I am currently working on a side business and as well as getting with a reputable company for a career. thank you so much for creating this blog.

Great post once again! Just a high school student and I’m glad to know what I have ahead of me (paying the toll). At least I’m one of the few that know what I’m getting into after high school. Excited to see the new product that is coming! Thanks WSPs

All business are basically services so you need to go out and perform the service for someone.
Do it for free up front and then as you gain traction / reputation, put a price on it.

FB ads should promote an already-successful service (Soccer mom loses 13lbs Overnight with NEW Amazon super-food / Make $15,000 online blogging like Gerald who turned his passion for dogs into a profitable online business).

I once had a guy come to me, he’d made basically every mistake in the book, and he was trying to hustle to get his life back on track.

He was struggling with the idea that he “couldn’t believe he was at this point at 27”.

He was having a hard time accepting that he had to learn certain basic skills and then build on that foundation if he was every going to be successful.

At the time I called it “Life Debt”, explaining that while he was making mistakes in his late teens and early twenties, others were putting the in the time to get better.

That’s why they were ahead of him.

It was hard for him, ego-wise, to accept it, but when I explained to him that way he resolved to get better (the same way you say “add 15 years to the milestones”).

Now he’s at a much better place, financially and otherwise, because he put in the work.

I wanted to share that with you as a bit of encouragement. As WSP said, it’ll be tough but it’s doable.

And another point which you may or may not have been considering with this, the decline in energy as you age, if you follow the advice here and “do the opposite” of what most 40 year olds do and maintain your fitness, you’ll be at least on the level of the average 25 year old Regular.

Will be 28 in a few months. Selling self created digital products online. Making 5-8k per month depending on rankings in google. Niche has potential for $30k per month profits with my plans for upsell products and heading into paid traffic too. Not from US and living abroad long term with offshore company setup so 0 income tax. Online biz should be fairly passive by end of 2018.

Got about $70k saved up and planning on getting into value investing when I hit about $150k. Next book on reading list “the intelligent investor”.

Not exactly business related but I will address something WSP talked about a while back. It has to do with breaking into IB and wall street on a non-traditional path.

You guys listed out an MBA as an option on one of your very old posts but also said something along the lines of “good luck if you want to work in finance in your 30s”. The way I see it, in some cases if you didn’t do life right like WSP recommended and found this site after the age of 22, it does seem like working on WS and getting that good MBA can provide benefits in the future.

I mean you will be behind in life, I feel, if you start a new career in your 30s as opposed to someone that did it right in their early 30s but it seems justifiable to break into IB as an associate.

Just my view, a teacher or someone who worked a less prestigious job in their 20s could benefit from this route from the knowledge they acquire as well as the possible connections they make, it might actually help them on their business venture.

Paying the life toll before you can expect more from life, or the similar concept of driving yourself until you burn out once in your twenties so you can know your limits and develop more profitable work habits later – this is one of my favourite themes you share. It reminds me of a passage from Hagakure, which is also a book I think you and any WSP readers would appreciate for its sound advice:

Shida Kichinosuke said, “At first it is an impressive thing to run until one is breathless. But it is an extraordinarily good feeling when one is standing around after the running. More than that, it is even better to sit down. More than that, it is even better to lie down. And more than that, to put down a pillow and sleep soundly is even better. A man’s whole life should be like this. To exert oneself to a great extent when one is young and then to sleep when he is old or at the point of death is the way it should be. But to first sleep and then exert oneself . . . Or To exert oneself to the end, and to end one’s whole life in toil is regrettable.”

Hey guys, 19 year old after a year in math changing to Engineering.
No major or minor, gotta pick my course. My option are Computer Science and Engineering or Electronic and Computer Engineering. The first is bachelors only the second Bachelor + Masters.

The first one is mostly software the second has more of a mix. Thing is from the first I know I’ll get it easier, there’s ton of jobs out there and opportunities, but feels too restrictive, just software. I’d like to create to solutions to various problems, not just software.

I was advised that if I wanted to go to banking to take the first, work and them MBA. But to be honest I’m not sure, I want money but would like to work in something of real impact.

I want to dedicate myself to my work, I know I might not be a genius but I’m smart. What do you advise?